TWI834690B - 用於防治無脊椎動物害蟲之異噁唑啉化合物 - Google Patents

Info

Publication number

TWI834690B

TWI834690B TW108125050A TW108125050A TWI834690B TW I834690 B TWI834690 B TW I834690B TW 108125050 A TW108125050 A TW 108125050A TW 108125050 A TW108125050 A TW 108125050A TW I834690 B TWI834690 B TW I834690B

Authority

TW

Taiwan

Prior art keywords

compound

formula

alkyl

methyl

trifluoromethyl

Prior art date

2018-07-18

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• 241000607479 Yersinia pestis Species 0.000 title claims abstract description 94
• 150000002547 isoxazolines Chemical class 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 1217
• 239000000203 mixture Substances 0.000 claims abstract description 294
• 238000000034 method Methods 0.000 claims abstract description 126
• 229910052739 hydrogen Inorganic materials 0.000 claims description 187
• 229910052801 chlorine Inorganic materials 0.000 claims description 147
• -1 C 1 -C 4 alkyl Chemical group 0.000 claims description 94
• 229910052731 fluorine Inorganic materials 0.000 claims description 83
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 60
• 239000007787 solid Substances 0.000 claims description 48
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 36
• 239000007788 liquid Substances 0.000 claims description 33
• 229910052799 carbon Inorganic materials 0.000 claims description 31
• 239000003795 chemical substances by application Substances 0.000 claims description 31
• 239000003085 diluting agent Substances 0.000 claims description 31
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 23
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 22
• 239000004094 surface-active agent Substances 0.000 claims description 22
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 21
• 150000001412 amines Chemical class 0.000 claims description 21
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
• 125000001424 substituent group Chemical group 0.000 claims description 19
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 17
• AUBHKIQOWQCHQD-UHFFFAOYSA-N 1-benzothiophene-4-carboxamide Chemical compound NC(=O)C1=CC=CC2=C1C=CS2 AUBHKIQOWQCHQD-UHFFFAOYSA-N 0.000 claims description 13
• 239000004009 herbicide Substances 0.000 claims description 12
• 229910052736 halogen Inorganic materials 0.000 claims description 11
• 150000002367 halogens Chemical class 0.000 claims description 11
• 229910052760 oxygen Inorganic materials 0.000 claims description 10
• 239000000575 pesticide Substances 0.000 claims description 9
• 239000000417 fungicide Substances 0.000 claims description 8
• 239000005645 nematicide Substances 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 7
• 241001465754 Metazoa Species 0.000 claims description 6
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 5
• 230000000844 anti-bacterial effect Effects 0.000 claims description 4
• 239000003899 bactericide agent Substances 0.000 claims description 4
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
• XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 3
• YOZUQPUWNYRWNX-UHFFFAOYSA-N N-cyclopropyl-7-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-1-benzothiophene-4-carboxamide Chemical compound C1(CC1)NC(=O)C1=CC=C(C=2SC=CC=21)C1=NOC(C1)(C(F)(F)F)C1=CC(=CC(=C1)Cl)Cl YOZUQPUWNYRWNX-UHFFFAOYSA-N 0.000 claims description 3
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
• 125000001153 fluoro group Chemical group F* 0.000 claims description 3
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 2
• 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 2
• TYDLCMMLQWEVSN-UHFFFAOYSA-N N-(1-cyanoethyl)-7-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-1-benzothiophene-4-carboxamide Chemical compound C(#N)C(C)NC(=O)C1=CC=C(C=2SC=CC=21)C1=NOC(C1)(C(F)(F)F)C1=CC(=CC(=C1)Cl)Cl TYDLCMMLQWEVSN-UHFFFAOYSA-N 0.000 claims description 2
• DPRVVKYMJFTPTH-UHFFFAOYSA-N N-[[4-[5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-1-benzofuran-7-yl]methyl]acetamide Chemical compound ClC=1C=C(C=C(C=1F)Cl)C1(CC(=NO1)C1=CC=C(C2=C1C=CO2)CNC(C)=O)C(F)(F)F DPRVVKYMJFTPTH-UHFFFAOYSA-N 0.000 claims description 2
• BPLREJJMWHSCCI-UHFFFAOYSA-N N-[[4-[5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4H-1,2-oxazol-3-yl]-1-benzothiophen-7-yl]methyl]acetamide Chemical compound ClC=1C=C(C=C(C=1F)Cl)C1(CC(=NO1)C1=CC=C(C=2SC=CC=21)CNC(C)=O)C(F)(F)F BPLREJJMWHSCCI-UHFFFAOYSA-N 0.000 claims description 2
• 238000006467 substitution reaction Methods 0.000 claims 1
• JXASPPWQHFOWPL-UHFFFAOYSA-N Tamarixin Natural products C1=C(O)C(OC)=CC=C1C1=C(OC2C(C(O)C(O)C(CO)O2)O)C(=O)C2=C(O)C=C(O)C=C2O1 JXASPPWQHFOWPL-UHFFFAOYSA-N 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 189
• 239000000460 chlorine Substances 0.000 description 163
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 82
• 235000019439 ethyl acetate Nutrition 0.000 description 64
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 61
• 241000196324 Embryophyta Species 0.000 description 58
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
• 239000011541 reaction mixture Substances 0.000 description 43
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 38
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
• 238000006243 chemical reaction Methods 0.000 description 35
• 239000000243 solution Substances 0.000 description 34
• 244000038559 crop plants Species 0.000 description 33
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 32
• 230000015572 biosynthetic process Effects 0.000 description 30
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
• 238000009472 formulation Methods 0.000 description 29
• 238000002360 preparation method Methods 0.000 description 28
• 239000000047 product Substances 0.000 description 28
• 238000003786 synthesis reaction Methods 0.000 description 28
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
• 239000002904 solvent Substances 0.000 description 26
• 238000011282 treatment Methods 0.000 description 26
• 238000005481 NMR spectroscopy Methods 0.000 description 25
• 239000003208 petroleum Substances 0.000 description 25
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 22
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
• 230000009418 agronomic effect Effects 0.000 description 21
• 125000002947 alkylene group Chemical group 0.000 description 20
• 239000002689 soil Substances 0.000 description 19
• 238000004458 analytical method Methods 0.000 description 18
• 239000012267 brine Substances 0.000 description 18
• NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Aalpha Natural products C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 18
• 241000238876 Acari Species 0.000 description 17
• 239000000126 substance Substances 0.000 description 17
• 238000005160 1H NMR spectroscopy Methods 0.000 description 16
• 239000004480 active ingredient Substances 0.000 description 16
• 230000008878 coupling Effects 0.000 description 16
• 238000010168 coupling process Methods 0.000 description 16
• 238000005859 coupling reaction Methods 0.000 description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
• 241000894006 Bacteria Species 0.000 description 15
• JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 15
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
• 230000000967 entomopathogenic effect Effects 0.000 description 15
• 230000001965 increasing effect Effects 0.000 description 15
• 229910052938 sodium sulfate Inorganic materials 0.000 description 15
• 235000011152 sodium sulphate Nutrition 0.000 description 15
• ZFHGXWPMULPQSE-UKSCLKOJSA-N (Z)-(1R)-cis-tefluthrin Chemical compound FC1=C(F)C(C)=C(F)C(F)=C1COC(=O)[C@H]1C(C)(C)[C@H]1\C=C(/Cl)C(F)(F)F ZFHGXWPMULPQSE-UKSCLKOJSA-N 0.000 description 14
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 14
• 241000700605 Viruses Species 0.000 description 14
• 230000000694 effects Effects 0.000 description 14
• 229910052757 nitrogen Inorganic materials 0.000 description 14
• 239000012044 organic layer Substances 0.000 description 14
• 239000000377 silicon dioxide Substances 0.000 description 14
• 241001124076 Aphididae Species 0.000 description 13
• 241000233866 Fungi Species 0.000 description 13
• 241000238631 Hexapoda Species 0.000 description 13
• 240000008042 Zea mays Species 0.000 description 13
• 235000002017 Zea mays subsp mays Nutrition 0.000 description 13
• 125000004076 pyridyl group Chemical group 0.000 description 13
• 239000005660 Abamectin Substances 0.000 description 12
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
• 241000258937 Hemiptera Species 0.000 description 12
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
• DVBUIBGJRQBEDP-UHFFFAOYSA-N cyantraniliprole Chemical compound CNC(=O)C1=CC(C#N)=CC(C)=C1NC(=O)C1=CC(Br)=NN1C1=NC=CC=C1Cl DVBUIBGJRQBEDP-UHFFFAOYSA-N 0.000 description 12
• 235000013399 edible fruits Nutrition 0.000 description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
• 229910052763 palladium Inorganic materials 0.000 description 12
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 12
• 241000254173 Coleoptera Species 0.000 description 11
• 239000005903 Gamma-cyhalothrin Substances 0.000 description 11
• 125000000217 alkyl group Chemical group 0.000 description 11
• OMFRMAHOUUJSGP-IRHGGOMRSA-N bifenthrin Chemical compound C1=CC=C(C=2C=CC=CC=2)C(C)=C1COC(=O)[C@@H]1[C@H](\C=C(/Cl)C(F)(F)F)C1(C)C OMFRMAHOUUJSGP-IRHGGOMRSA-N 0.000 description 11
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• 230000012010 growth Effects 0.000 description 11
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
• 230000000975 bioactive effect Effects 0.000 description 10
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• KAATUXNTWXVJKI-QPIRBTGLSA-N [(s)-cyano-(3-phenoxyphenyl)methyl] 3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-QPIRBTGLSA-N 0.000 description 8
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• FMPFURNXXAKYNE-UHFFFAOYSA-N [2-ethyl-3,7-dimethyl-6-[4-(trifluoromethoxy)phenoxy]quinolin-4-yl] methyl carbonate Chemical compound C1=C2C(OC(=O)OC)=C(C)C(CC)=NC2=CC(C)=C1OC1=CC=C(OC(F)(F)F)C=C1 FMPFURNXXAKYNE-UHFFFAOYSA-N 0.000 description 8
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